Professional Documents
Culture Documents
Amiloxate (USAN, rINN) 3. Hughes CG. Oral PABA and vitiligo. J Am Acad Dermatol 1983; Avobenzone (USAN, rINN)
9: 770.
Amiloxato; Amiloxatum; E-1000; Isoamyl p-Methoxycinnamate. 4. Worobec S, LaChine A. Dangers of orally administered para- Avobenzona; Avobenzonum; Butylmethoxydibenzoylmethane;
Isopentyl p-methoxycinnamate; 3-(4-Methoxyphenyl)-2-prope- aminobenzoic acid. JAMA 1984; 251: 2348. 4-tert-Butyl-4-methoxydibenzoylmethane. 1-(p-tert-Butylphe-
noic acid 3-methylbutyl ester. Pharmacokinetics nyl)-3-(p-methoxyphenyl)-1,3-propanedione; 1-[4-(1,1-dimeth-
If given orally, aminobenzoic acid is absorbed from the gastroin- ylethyl)phenyl]-3-(4-methoxyphenyl)-1,3-propanedione.
C 15 H 20O 3 = 248.3. testinal tract. It is metabolised in the liver and excreted in the
urine as unchanged drug and metabolites.
C AS 71617-10-2.
C 20 H 22 O 3 = 310.4.
Uses and Administration
Aminobenzoic acid is applied topically as a sunscreen (p.1576). C AS 70356-09-1.
O Aminobenzoic acid and its derivatives effectively absorb light
throughout the UVB range but absorb little or no UVA light (for
definitions, see p.1580). Aminobenzoate sunscreens may there- CH3
H3C O O fore be used to prevent sunburn, but are unlikely to prevent drug- H 3C
related or other photosensitivity reactions associated with UVA O
CH3 H 3C CH3
light; combination with a benzophenone may give some added
H 3C protection against such photosensitivity.
Aminobenzoic acid has sometimes been included as a member
NOTE. Neo-Heliopan E 1000 is a trade name that has been used of the vitamin-B group, but deficiency of aminobenzoic acid in
man or animals has not been found.
O O
for amiloxate.
Pharmacopoeias. In US. Aminobenzoic acid has been used with bentiromide (p.2264) in
the PABA or BTPABA test of pancreatic function. NOTE.Escalol 517, Eusolex 9020, Neo-Heliopan 357, and Parsol
USP 31 (Amiloxate). Store in airtight containers. 1789 are trade names that have been used for avobenzone.
Preparations
Profile Pharmacopoeias. In US.
USP 31: Aminobenzoic Acid Gel; Aminobenzoic Acid Topical Solution.
Amiloxate, a substituted cinnamate, is a sunscreen (p.1576) with USP 31 (Avobenzone). M.p. 81 to 86. Store in airtight con-
actions similar to those of octinoxate (p.1608). It is effective Proprietary Preparations some preparations are listed in Part 3.
tainers. Protect from light.
against UVB light (for definitions, see p.1580).
Preparations Profile
Ammonium Lactate (USAN) Avobenzone is a substituted dibenzoylmethane used by topical
Proprietary Preparations some preparations are listed in Part 3. application as a sunscreen (p.1576). Dibenzoylmethanes absorb
Amonio, lactato de; BMS-186091.
light in the UVA range (for definitions, see p.1580) and may
therefore be used with other sunscreens that absorb UVB light to
C 3 H 9 NO 3 = 107.1. prevent sunburn; they will also provide some protection against
Aminobenzoic Acid C AS 52003-58-4. drug-related or other photosensitivity reactions associated with
Acide 4-Aminobenzoque; Acidum 4-aminobenzoicum; Amben; ATC Vet QA16QA04. UVA light.
4-Aminobensoesyra; 4-Aminobentsoehappo; 4-aminobenzoe-
_ Contact and photocontact allergic dermatitis has occasionally
sav; Aminobenzoico, cido; 4-Aminobenzoine ru gtis; Kwas 4- been reported with the topical use of dibenzoylmethane sun-
aminobenzoesowy; Kyselina 4-aminobenzoov; PAB; PABA; Pa- O NH4+
screens.
bacidum; Para-aminobenzoic Acid; Vitamin Bx; Vitamin H. 4- O-
Aminobenzoic acid. Preparations
H3C
Proprietary Preparations numerous preparations are listed in
C 7 H 7 NO 2 = 137.1. OH Part 3.
C AS 150-13-0.
ATC D02BA01. Profile
ATC Vet QD02BA01. Ammonium lactate is a humectant applied as a cream or lotion
containing 12% lactic acid neutralised with ammonium hydrox- Azelaic Acid (USAN, rINN)
ide. It is used in the treatment of dry scaly conditions of the skin
O OH including ichthyosis. Adverse effects of topical ammonium lac- Acide azlaque; cido azelaico; Acidum azelaicum; Anchoic acid;
tate preparations include transient erythema, burning, and sting- Atselaiinihappo; Azelaik Asit; Azelainsyra; Lepargylic acid; ZK-
ing. Treated areas may be more sensitive to sunlight and expo- 62498. Nonanedioic acid; Heptane-1,7-dicarboxylic acid.
sure should be minimised.
Preparations
C 9 H 16 O 4 = 188.2.
Proprietary Preparations (details are given in Part 3)
Arg.: Lacto-Cev; Lactrex; Braz.: Lac-Hydrin; Canad.: Lac-Hydrin; Chile: C AS 123-99-9.
Kerapil; Topilact 12; Fr.: Kerapil; Malaysia: Lanate; Mex.: Lac-Hydrin;
NH2 NZ: Lac-Hydrin; Lanate; Singapore: Lac-Hydrin; Lanate; USA: Amlactin; ATC D10AX03.
Geri-Hydrolac; Kerasal AL; Lac-Hydrin; LAC-Lotion. ATC Vet QD10AX03.
Pharmacopoeias. In Eur. (see p.vii) and US. Multi-ingredient: Arg.: Clobeplus; Clobesol LA; Lactiderm; Lactiderm
Ph. Eur. 6.2 (4-Aminobenzoic Acid; Aminobenzoic Acid BP HC; Lacto-Cev Zn; Urecrem Hidro; Braz.: Lactrex; Chile: Ichtyosoft;
KPL; Lactrex; Queratopil; Fr.: I-Soft; Ichtyosoft; Keralac Plus; Zeniac
2008). White or slightly yellow crystalline powder. Slightly sol- LP Fort; Zeniac LP; Zeniac; Indon.: Exfoliac; Ital.: Alfa Acid; Ipso Urea; O O
uble in water; freely soluble in alcohol; it dissolves in dilute so- Mex.: Lactrex; Port.: Lactonico; Venez.: Lactrex.
lutions of alkali hydroxides. Protect from light.
USP 31 (Aminobenzoic Acid). White or slightly yellow, odour- HO OH
less crystals or crystalline powder. It discolours on exposure to
air or light. Slightly soluble in water and in chloroform; freely
Arbutin
soluble in alcohol and in solutions of alkali hydroxides or car- Arbutoside; Arbutyna; Beta-arbutin; Ursin. 4-Hydroxyphenyl-D- Adverse Effects and Precautions
bonates; sparingly soluble in ether. Store in airtight containers. glucopyranoside. Topical application of azelaic acid may produce a tran-
Protect from light. sient skin irritation such as burning, stinging, pruritus,
Adverse Effects and Precautions C 12 H 16 O 7 = 272.3.
C AS 497-76-7 (beta-arbutin); 84380-01-8 (alpha-ar- dryness, and scaling. It is usually mild and disappears
Adverse skin reactions such as local irritation and contact derma- on continued treatment, but in a few patients the irrita-
titis have been reported after the topical use of aminobenzoate butin).
sunscreens. Aminobenzoate sunscreens should not be used by tion may persist, requiring reduced frequency of appli-
those with a history of photosensitivity or hypersensitivity reac- cation or temporary suspension of treatment. There
tions to structurally related drugs such as sulfonamides, thiazide HO have been rare reports of hypopigmentation, rash, and
diuretics, and ester-type local anaesthetics. photosensitivity. Azelaic acid should not be applied to
Aminobenzoic acid may stain clothing. O OH
O the eyes, mouth, or other mucous membranes.
Allergic and photoallergic contact dermatitis have been report- OH
ed after topical use of aminobenzoic acid or its esters.1 Early re- Uses and Administration
OH
ports of such reactions led to the removal of these compounds
from sunscreen preparations (many are now described as PA- OH Azelaic acid inhibits the growth of Propionibacterium
BA-free), although padimate O still appears to be widely used.2 spp. and reduces keratinisation. It is used in the topical
Patients allergic to aminobenzoic acid may also react to structur- Profile treatment of mild to moderate inflammatory acne
ally related allergens such as para-aminobenzoic acid ester an- Arbutin is a glycosylated derivative of hydroquinone (p.1598) (p.1577) and for the inflammatory papules and pus-
aesthetics, sulfonamides, and paraphenylenediamine in hair extracted from bearberry (p.2263) and similar plants. It is used
tules of mild to moderate rosacea (p.1583). It has also
dyes.1,2 topically in concentrations of 1 to 5% as a depigmenting agent
for the skin in hyperpigmentation disorders. The higher concen- been tried in hyperpigmentary skin disorders such as
Skin reactions (vitiligo) have also been reported with oral ami-
nobenzoic acid3 and the adverse effects associated with the trations may lead to a paradoxical hyperpigmentation. melasma, and in malignant melanoma.
former use of high oral doses for various conditions have been Alpha-arbutin has been used similarly. In the treatment of acne azelaic acid is applied twice
highlighted.4 Preparations daily for up to 6 months as a 20% cream or 15% gel.
1. Scheuer E, Warshaw E. Sunscreen allergy: A review of epidemi- Proprietary Preparations (details are given in Part 3)
ology, clinical characteristics, and responsible allergens. Derma- Improvement usually occurs within four weeks.
titis 2006; 17: 311. Correction. ibid.; 162. Multi-ingredient: Arg.: Cellskinlab Phyto Spot; Melasoft; Chile: Phyto
2. Mackie BS, Mackie LE. The PABA story. Australas J Dermatol
Corrective Gel; Phyto Spot; Port.: Despigmentante. For the treatment of mild to moderate rosacea, a 15%
1999; 40: 513. gel should be applied to the affected area twice daily
The symbol denotes a preparation no longer actively marketed The symbol denotes a substance whose use may be restricted in certain sports (see p.vii)
1590 Dermatological Drugs and Sunscreens
for a period of up to 12 weeks. Improvement usually Preparations that has a device for the release of excess pressure. Unused ma-
occurs in 4 to 8 weeks. Proprietary Preparations (details are given in Part 3) terial should not be returned to its original container but should
Austria: Regranex; Canad.: Regranex; Cz.: Regranex; Fr.: Regranex; Ger.: be destroyed by the addition of sodium hydroxide solution
References. Regranex; Gr.: Regranex; Israel: Regranex; Mex.: Regranex; Neth.: Re- (10%). Destruction can be considered to be complete if the addi-
granex; Port.: Regranex; Spain: Regranex; Switz.: Regranex; UK: Regran- tion of a crystal of potassium iodide does not result in the release
1. Fitton A, Goa KL. Azelaic acid: a review of its pharmacological ex; USA: Regranex.
properties and therapeutic efficacy in acne and hyperpigmentary of free iodine after acidification with dilute hydrochloric acid.
skin disorders. Drugs 1991; 41: 78098. Multi-ingredient: USA: GEM 21S. Protect from light.
2. Breathnach AS. Melanin hyperpigmentation of skin: melasma, USP 31 (Hydrous Benzoyl Peroxide). It contains not less than
topical treatment with azelaic acid, and other therapies. Cutis 65% and not more than 82% of anhydrous benzoyl peroxide with
1996; 57 (suppl): 3645.
Bemotrizinol (USAN, rINN) a water content of about 26%. The hydrous form is a white gran-
3. Elewski B, Thiboutot D. A clinical overview of azelaic acid.
Cutis 2006; 77 (suppl): 1216. Bmotrizinol; Bemotrizinolum; BEMT; Bis-ethylhexyloxyphenol ular powder with a characteristic odour. Sparingly soluble in wa-
4. Del Rosso JQ. The use of topical azelaic acid for common skin
ter and in alcohol; soluble in acetone, in chloroform, and in ether.
Methoxyphenol Triazine; FAT-70884. 2,2-[6-(4-Methoxyphe-
disorders other than inflammatory rosacea. Cutis 2006; 77 (sup- Store in the original container, treated to reduce static charges.
nyl)-1,3,5-triazine-2,4-diyl]bis{5-[(2-ethylhexyl)oxy]phenol}. Unused material should not be returned to its original container
pl): 224.
5. Liu RH, et al. Azelaic acid in the treatment of papulopustular but should be destroyed by the addition of sodium hydroxide so-
rosacea: a systematic review of randomized controlled trials. C 38 H 49N 3 O 5 = 627.8. lution (10%). Destruction can be considered to be complete if the
Arch Dermatol 2006; 142: 104752. C AS 187393-00-6. addition of a crystal of potassium iodide does not result in the re-
Preparations lease of free iodine.
Proprietary Preparations (details are given in Part 3) OCH